Evening Experiences

KEY WEST

Best Evening Experiences In Key West

Ranked by traveller popularity

The 10 most popular evening experiences in Key West. Here's what they actually deliver, who runs them, and what they cost.

10 Best Evening Experiences In Key West

Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - Your Route: Mallory Square, Fort Zachary Taylor, and Sunset Key Moments

1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

Most Popular★ 4.5

A 2-hour Key West sunset sail on a roomy catamaran with an open bar, sangria, hors d’oeuvres, and live local music.

“The captain and crew were extremely attentive to all of the passengers. They even brought drinks and horsdoeuvres to the passengers hanging out on the main deck who were watching the Amazing sunset. They even mingled with the everyone and helped take pictures when asked. This was a highlight of our time at Key West!!”

3,559 reviews2 hours (approx.)From $79.00by Sebago Key West

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Key West Sunset Cruise: Dinner, Live Music & Drinks Included

Key West Sunset Cruise: Dinner, Live Music & Drinks Included - The Tropical Buffet Dinner: What You’ll Actually Taste

Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset

Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset - Kayaking Through Mangroves: Calm Water, Real Wildlife Energy

3.Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset

★ 5.0

Half-day sailing, kayaking, and snorkeling off Key West, with wetsuits, reef wildlife, drinks and sunset options.

“This was out second time with Danger, and we really enjoyed both outings. Smaller crowds, lovely boat, informative guides, and great time on the water. I appreciated the use of wet suits, it was a thoughtful addition to the experience.”

1,683 reviews4 hours 30 minutes (approx.)From $115.00by Danger Charters

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Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - The Route: From Front Street Check-In to a Two-Hour Evening on the Water

4.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

★ 5.0

Small-group Key West sunset sail with a wine tasting, unlimited beer, and hors d’oeuvres, plus crew stories and a smoother pace for two hours.

“What an amazing experience! The wine was plentiful, the snacks were delicious, and the view of the water and sunset were unbeatable. Mary, James, and Connor were professional and friendly. All around absolutely worth doing this!”

1,366 reviews2 hours (approx.)From $125.00by Danger Charters

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Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses - Catamaran Echo and the 14-Passenger Advantage

5.Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

★ 5.0

Adults-only Key West sunset champagne cruise on a 14-passenger catamaran: unlimited wine, gourmet cheese, and Moët upgrades.

“This was such a wonderful experience. Having a small group made it even more special. The sunset was beautiful. The captain and crew were knowledgeable and hospitable. If you’re wondering if you should book this trip- you definitely should!”

954 reviews2 hours (approx.)From $108.91by Dolphin Echo Inc. (Catamaran Echo)

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Key West Sunset Sail with Live Music, Drinks and Appetizers

Key West Sunset Sail with Live Music, Drinks and Appetizers - Unlimited Drinks and Appetizers: What You Actually Get

Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included - Small-Group Sailing at Sea Level: The Feel on Deck

Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - Your Two-Hour Schedule: What Happens From Departure to Sunset

8.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

★ 5.0

Key West sunset on America 2.0: beer, wine, champagne, and plated hors d’oeuvres as you pass Fort Zachary and Mallory Square.

“Our captain, Janet was fantastic! She made sure our experience on her ship was perfect including the sunset. Her crew Jade, Milo & Heather were super efficient in not only tending to the ship’s duties but served their guests with a huge smile. Thanks for the great experience!🌞⛵️”

804 reviews2 hours (approx.)From $122.59by Classic Harbor Line

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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Meeting at 205 Elizabeth St and What That Means for Your Timing

Key West Champagne Sunset Catamaran Cruise

Key West Champagne Sunset Catamaran Cruise - The sunset route you’ll feel: Sebago Watersports to Mallory Square to Fort Zachary Taylor

10.Key West Champagne Sunset Catamaran Cruise

★ 4.5

Key West champagne sunset catamaran with beer, wine, champagne, sangria and light bites. 1.5 hours of captain-led views.

“So much fun and the crew is fantastic!! If you do nothing else, DO THIS! I really can’t say enough good things. It’s just a really good time.”

586 reviews1 hour 30 minutes (approx.)From $59.00by Sebago Key West

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After Dark